Caribbean Holidays
Enduring laidback charm
From family escapes to couples retreats and adults only hideaways, each handpicked hotel in our Caribbean portfolio has something for all. Picture endless white beaches, warm shallow waters and untouched rainforests, all wrapped up in a carnival atmosphere with smiling hospitality that welcomes you in.
Caribbean Islands
Caribbean Holidays
The white sandy beaches, lush tropical forests, crystal blue seas and friendly atmosphere of the Caribbean are the ideal combination for a relaxing and luxurious escape. Throughout the many Caribbean islands, there really is something for everyone. Whether it's the sun-soaked shores of Barbados, the sizzling cuisine of Antigua or the laid-back atmosphere of Jamaica, you will surely find the ideal spot for your holiday this year. You'll also find a great range of accommodation. Along with our all-inclusive resorts and intimate boutique hotels, we offer everything from private villas with maid service and cooking to barefoot beach huts.
Luxury Holidays to the Caribbean
If it's a luxury Caribbean holiday you're looking for, our destination experts offer a superb range of hotels to match your style. Whether you want a romantic honeymoon destination, an all-inclusive holiday for the family or a tranquil solo break, talk to our Caribbean travel team and plan a tropical getaway you'll never forget. Book now to take advantage of our range of direct deals with the area's best hotels, including Sandy Lane in Barbados, and Jade Mountain and Coconut Bay Beach Resort & Spa in St Lucia. And don’t miss the special prices our experts have arranged with our preferred hotel partners in the Caribbean, such as the popular Sandals Resorts in Antigua, Barbados, Grenada, Jamaica, St Lucia, The Bahamas and Turks & Caicos.
School Holidays in the Caribbean
We have limited availability to the Caribbean over the Christmas & New Year school holidays. Our Christmas special offers are exclusive to us, with early January inbounds available. We have holidays to Barbados, Antigua, Jamaica, and St Lucia, all with discounts for children and savings of up to 30%. Escape this winter and jet off to the sunny Caribbean for Christmas & New Year, plus find a host of other school holiday dates as far as Barbados, St Lucia, Cancun, and Antigua that let you beat the rush for places during peak times.
Book Early to Guarantee Your Caribbean Holiday Deals for 2025 & 2026
We have some great Caribbean holidays for 2025 & 2026 available with up to 60% savings on some hotels and generous early booking discounts on our flights. Look for deals using our onsite Holiday Search facility or call the Kenwood team. Our flights are booked with our preferred partners Virgin Atlantic and British Airways. For pre-booked seats, teen discounts and any tailor-made requirement for your holiday, call our advisors now and let us take care of the details.
Caribbean Weather
Even from space, the Caribbean’s shallow cays and coral lagoons loom impossibly blue – a testament to the archipelago’s invitingly warm waters – and illustrate the hot weather these islands are blessed with year-round. Welcome to one of the finest climates in the Americas. Cooling north-easterly trade winds moderate the Caribbean’s on-land temperatures to a tropical 24°C to 32°C at sea level, and these readings will tend not to fluctuate regardless of the time of day, month or season. Pretty predictable, but variations in temperature do occur at higher altitudes, with hilly regions being slightly cooler.
Rather than use a conventional four-season model to explain any meteorological variances, an understanding of the Caribbean’s weather patterns is probably best divided neatly into two: the rainy season – May to October – and the dry season, which corresponds to our winter. Don’t be discouraged though – even during the so-called rainy season, wet conditions fluctuate and showers can be short-lived. Leeward sides of mountainous islands are known to remain dry throughout. So, if you’re beach-ready and aching for some fun in the sun, the Caribbean is waiting to grace you with its gorgeous weather. The boxes are ticked for blue skies, clear waters and summer heat.
Special offers
The Verandah Antigua
Located next to a National Park, The Verandah Antigua is an adults only, eco-friendly oasis where lush gardens, a spa, tennis courts & watersports provide relaxation and leisure. As seen on hit channel 4 TV show, Made in Chelsea.
7 nights All Inclusive including Virgin Atlantic flights from £1,531 per person
Sea Breeze Beach House
- 50% saving
7 nights All Inclusive including Virgin Atlantic flights from £1,743 per person
Hard Rock Hotel & Casino Punta Cana
Indulge your inner rock star in paradise settings at Hard Rock Hotel & Casino Punta Cana. This exciting hotel caters for all with 11 swimming pools, kids-friendly and adults-only areas, nightclub and casinos.
7 nights All Inclusive including British Airways flights from £2,090 per person
Calabash Hotel
This sophisticated resort is perfectly suited to serve as your luxury Caribbean holiday home, from luxury spa treatments to restaurant-style breakfast on the beach.
7 nights Bed and Breakfast including Virgin Atlantic flights from £2,784 per person
Royalton Grenada, An Autograph Collection All-Inclusive Resort
- Up to 51% saving
7 nights All Inclusive including Virgin Atlantic flights from £1,514 per person
Casa de Campo Resort & Villas
Practically an oceanfront town in its own right, multi-award-winning Casa de Campo Resort & Villas is a 7,000-acre dream, featuring top golf courses, an equestrian centre, beach and incredible spa.
7 nights Room Only including British Airways flights from £2,077 per person
Spice Island Beach Resort
Renowned for its unparalleled location on the world-famous Grand Anse Beach, this is as much the perfect family getaway as it is a romantic retreat or watersports holiday.
7 nights Bed and Breakfast including Virgin Atlantic flights from £2,889 per person
Sandals Grande Antigua
- Complimentary Airport Transfers
7 nights All Inclusive including Virgin Atlantic flights from £1,770 per person
Carlisle Bay
- Complimentary Half Board
- 30% saving
7 nights Half Board including Virgin Atlantic flights from £2,327 per person
Blue Waters Resort and Spa
- Up to 25% saving
7 nights Bed and Breakfast including Virgin Atlantic flights from £2,090 per person
St James’s Club & Villas
St James’s Club & Villas is a popular resort year-round due to its great range of watersports such as catamaran tours, snorkelling and surfing as well as a fun kids club.
7 nights All Inclusive including Virgin Atlantic flights from £1,416 per person
Royalton CHIC Antigua, An Autograph Collection All-Inclusive Resort
- Up to 43% saving
7 nights All Inclusive including Virgin Atlantic flights from £1,626 per person
The Crane Resort
- 40% saving
- Stay 7 Pay 5
7 nights Bed and Breakfast including Virgin Atlantic flights from £1,140 per person
The Club Barbados Resort & Spa
This all inclusive, adults-only 4-star resort is situated on the magnificent West Coast of Barbados and offers the chance for travellers to partake in a number of watersport activities and live entertainment.
7 nights All Inclusive including Virgin Atlantic flights from £1,457 per person
The Rockley
- Up to 35% saving
7 nights Bed and Breakfast including Virgin Atlantic flights from £1,225 per person
Margaritaville Beach Resort
- Up to 58% saving
7 nights Room Only including Virgin Atlantic flights from £1,721 per person
British Colonial Nassau
A tranquil haven in Nassau. This hotel is as much a part of Bahamian history as the pirates who once sailed the surrounding seas.
7 nights Room Only including Virgin Atlantic flights from £1,860 per person
The Fives Oceanfront
- Resort credit Coupon US$555 per room per stay
7 nights Room Only including British Airways flights from £1,181 per person
Secrets Moxche Playa Del Carmen
A paradise bordered by magnificent tropical vegetation and a beautiful sea, your stay here has an Unlimited-Luxury® experience beyond compare.
7 nights All Inclusive including British Airways flights from £2,093 per person
Dreams Tulum Resort & Spa
The Dreams Tulum Resort & Spa is a deluxe resort located just minutes away from the ancient Mayan pyramids which offers guests luxury and elegant charm.
7 nights All Inclusive including British Airways flights from £1,432 per person
Hard Rock Hotel Riviera Maya
The Hard Rock Hotel Riviera Maya offers plenty of opportunity for the wild at heart. Discover Mexico's best-kept secret in an ambience of total luxury and indulgence.
7 nights All Inclusive including British Airways flights from £1,735 per person
Hard Rock Cancun
With all the bohemian charm of a rock 'n' roll theme hotel, this is a luxurious resort for adults seeking the ideal wedding or honeymoon destination, but it's just as good for families.
7 nights All Inclusive including British Airways flights from £1,723 per person
AVA Resort Cancun
An All Inclusive paradise on Cancun's sunny shores, this beautiful resort offers all the luxury you could dream of.
7 nights All Inclusive including British Airways flights from £1,791 per person
Zoëtry Agua Punta Cana
Luxury boutique resort on Dominican Republic's picturesque north-east coast provides you with top-quality amenities and a very relaxing Caribbean ambience.
7 nights All Inclusive including British Airways flights from £2,411 per person
Dreams Dominicus La Romana
Enjoy a wealth of activities offered by Dreams Dominicus La Romana, from a PADI-certified diving centre to a tranquil spa to a gorgeous white-sand beach.
7 nights All Inclusive including British Airways flights from £1,610 per person
Dreams Macao Beach Punta Cana Resort & Spa
Unwind on one of the Caribbean’s most spectacular beaches and discover Unlimited-Luxury with endless activities and facilities, five-star service & unlimited a la carte dining.
7 nights All Inclusive including British Airways flights from £1,779 per person
Dreams Royal Beach Punta Cana
Sophisticated amenities, deluxe pools, outdoor cinema on the beach - all this and more awaits you at this stylish all-inclusive resort.
7 nights All Inclusive including British Airways flights from £1,715 per person
S Hotel Montego Bay
- 25% saving
7 nights All Inclusive including British Airways flights from £1,869 per person
Moon Palace Jamaica
- Complimentary Return Airport Transfers from Montego Bay
- Kids & Teens Stay Free
7 nights All Inclusive including Virgin Atlantic flights from £1,672 per person
Couples Swept Away
- Complimentary Standard Transfers (Montego Bay Airport Only)
- Stay 14 Pay 12
7 nights All Inclusive including Virgin Atlantic flights from £1,895 per person
Coconut Bay Beach Resort & Spa
- Up to 65% saving
- Standard Transfers
7 nights All Inclusive including British Airways flights from £1,851 per person
The Landings Resort and Spa
- Up to 35% saving
7 nights Bed and Breakfast including British Airways flights from £1,781 per person
Sandals Saint Vincent and the Grenadines
- Internal Flights
- Complimentary Airport Transfers
7 nights All Inclusive including Virgin Atlantic flights from £2,147 per person
Bequia Beach Hotel
- Up to 40% saving
7 nights Bed and Breakfast including Virgin Atlantic flights from £1,293 per person
Coco Reef Resort & Spa
- Up to 40% saving
7 nights Bed and Breakfast including Virgin Atlantic flights from £1,184 per person
Dreams Curaçao Resort Spa & Casino
A stay at Dreams Curaçao Resort, Spa & Casino is a way to unwind whilst in tropical Caribbean paradise.
7 nights All Inclusive including American Airlines flights from £1,554 per person
Zoëtry Curaçao Resort & Spa
An oasis of peace and tranquillity set on the beautiful island of Curaçao. Enjoy luxurious suites, a la carte restaurants, and fantastic spa facilities.
7 nights All Inclusive including American Airlines flights from £1,744 per person
Sunscape Curaçao Resort, Spa & Casino
Enjoy stunning rooms and suites, unlimited dining and drinking, and endless activities at all-inclusive, family-friendly Sunscape Curaçao Resort, Spa & Casino.
7 nights All Inclusive including American Airlines flights from £1,426 per person
Caribbean Holiday Types
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